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Ghazi Daradkeh1,2 and Musthafa Mohamed Essa1* 1Sultan Qaboos University, Muscat, Oman; 2Hamad Medical Corporation, Doha, Qatar

16.1 Botany RH (Cantwell, 2001) and of over 12 days in a cold store at 0–2°C and RH 95–97% 16.1.1 Introduction (Lisiewska et al., 1997). However, at 18–20°C and 85–90% RH, it can only be stored for 3 days (Lisiewska et al., 1997). As already Parsley (Petroselinum crispum) is a herb belong- noted, parsley can be cold stored, but it is ing to the (formerly Umbelliferae) sensitive to chilling injury. family (Fig. 16.1). It is native to the Mediterra- nean region where it is found in the wild form. It is mostly grown outdoors and is sea- sonally harvested (Navazio, 2012). Parsley is a leafy vegetable, rich in many biologically 16.1.2 History active compounds, and its name (Petroselinum) is derived from the Greek for ‘rock celery’; it The botanical name Petroselinum is derived can be distinguished from other leafy green from the Greek words ‘petros’, meaning stone herbs by its unique aroma. In sunny areas (it grows on rocky hillsides) and ‘selinon’ with suitable environmental conditions – in a (parsley or celery). Parsley is mentioned in humid soil with a pH of 5.3–7.3 – parsley may Greek historical records as being used for grow up to 60–120 cm tall (Navazio, 2012). cheering sportsmen by wearing crowns made Parsley is sensitive to water stress, espe- of parsley; wreaths made from parsley were cially if it is planted in the summer and at the also used to adorn graves. Parsley was also used end of spring, and to increase production and in Roman rituals. There are reports of it being improve quality, a permanent source of water sprinkled over dead bodies to remove the should be provided. Both growth stage and smell too. Parsley is used in the Jewish cele- parsley type determine the susceptibility of bration of the Passover as well. It is men- the to water stress (Petropoulos et al., tioned as one of the plants in the gardens of 2006; Najla et al., 2012). Charlemagne and Catherine de Medici, and Fresh parsley has been reported to have there is a rumour that parsley was popular- a storage life of 1–2 months at 0°C and 95–100% ized in by Catherine de Medici.

*Corresponding author, e-mail: [email protected]

© CAB International 2016. Leafy Medicinal Herbs: Botany, Chemistry, Postharvest Technology and Uses (eds D.C.P. Ambrose et al.) 189 190 G. Daradkeh and M.M. Essa

Fig. 16.1. A parsley and leaves.

16.1.3 Location and zinc; it is an important dietary component for strengthening bone due to its high con- Parsley is believed to be native to southern tent of boron and fluorine, and also contains , but it is now found throughout the iron and calcium in an absorbable form world. It has been grown in Britain since at (Table 16.1). least the 16th century. Parsley has now become naturalized throughout Europe, North Amer- ica, the West Indies, and Lebanon. 16.2.2 Phytochemistry

16.1.4 Morphology Parsley has anti-inflammatory, antimicrobial, diuretic and hypoglycaemic properties due There are three varieties of parsley: curly- to its content of essential oil and phenolic leaved or common parsley, Italian or flat-­ compounds (Taiz and Zeiger, 1998). Yoshi- leaved parsley and root (Hamburg) parsley, kawa et al. (2000) reported several flavone which is grown for its edible root. The leaves glycosides with oestrogenic activity from are compound, alternately arranged, and the aerial parts of parsley, along with a new are divided into two to three leaflets and the monoterpene glucoside, petroside. plant can grow to over 1 m tall, and as an The leaves contain 0.04–0.4% of volatile annual (in tropical regions) or a biennial oil, and this includes as major constituents crop (in temperate areas). The typical flower- α-pinene, β-pinene, myrcene, β-phellandrene, ing period is in the warmer months and the 1,3,8-p-menthatriene and myristicin (Charles, ideal temperature for pollination and seed 2004). The aroma of parsley is due to the pres- production is 29–30°C (Teuscher, 2005). ence of terpenes, which are toxic to many The roots are a faint yellow colour and insects. Myristicin (see Fig. 16.2) is a toxic carrot shaped. They can grow up to 20 cm in phenylpropene/allylbenzene compound (also length and 5 cm in width. Hamburg root pars- known as 5-methoxysafrole) and has hallu- ley has larger roots and is commonly used cinogenic properties, acting as a psycho- in European cuisine (Teuscher, 2005). active at high intake levels (Hallström and Thuvander, 1997). The seeds contain 2–8% of volatile oil 16.2 Chemistry and 13–22% of fixed oil, and the major compounds found in the volatile oil are 16.2.1 Chemical (nutritional) α-pinene, β-pinene, myristicin, , composition 2,3,4,5-­tetramethoxy-allylbenzene and apiol (Charles, 2004). Apiol, a phenylpropene Parsley is a ‘powerhouse’ of nutrition, and (also known as apiole and as dimethoxysaf- is rich in B vitamins, vitamin C, β-carotene role; see Fig. 16.3), is responsible for the Parsley 191

Table 16.1. Nutritional value of parsley for one serving (60 g). Adapted from SELFNutritionData (2016); original source USDA National Nutrient Database for Standard Reference, Release 21 (USDA ARS, 2008).

Nutrient Amount

Calories 21.6 Vitamins From carbohydrate 13.3 Vitamin A 5055 IU From fat 4.0 Vitamin B

From protein 4.3 Thiamine (B1) 0.1 mg

From 0.0 Riboflavin (B2) 0.1 mg

Carbohydrates Niacin (B3) 0.8 mg

Total carbohydrate 3.8 g Vitamin B6 0.1 mg

Dietary fibre 2.0 g Pantothenic acid (B5) 0.2 mg a Starch ~ Folate (B9) 91.2 mcg

Sugar 0.5 g Vitamin B12 0.0 mcg Fats and fatty acids Vitamin C 79.8 mg Total fat 0.5 g Vitamin D ~ Saturated fat 0.1 g Vitamin E (α-tocopherol) 0.4 mg Monounsaturated fat 0.2 g Vitamin K 984 mcg Polyunsaturated fat 0.1 g Choline 7.7 mg Omega-3 fatty acids 4.8 mg Betaine ~ Omega-6 fatty acids 69.0 mg Minerals Protein and amino acids Calcium 82.8 mcg Protein 1.8 g Iron 3.7 mg Sterols Magnesium 30.0 mg Cholesterol 0.0 mg Phosphorus 34.8 mg Phytosterols 3.0 mg Potassium 332 mg Other constituents Sodium 33.6 mg Alcohol 0.0 mg Zinc 0.1 mg Ash 1.3 g Copper 0.1 mg Caffeine 0.0 mg Manganese 0.1 mg Theobromine 0.0 mg Selenium 0.1 mcg Water 52.6 g Fluoride ~ aSignifies missing or incomplete data.

OCH3

H2C O O

O O

OCH3 OCH3

Fig. 16.2. The chemical structure of myristicin. Fig. 16.3. The chemical structure of apiol. Adapted Adapted from Zhang et al., 2006. from Zhang et al., 2006. abortifacient properties of parsley, and the 2003), while apiin (-7-apioglucoside; herb may be used to treat menstrual dis- see Fig. 16.4) makes up to 0.2–1.6% of the orders (Castleman, 2009). roots (Taiz and Zeiger, 1998). Parsley roots contain 0.2–0.75% of essen- Table 16.2 compares the constituents of tial oil, which has as its main components commercial samples of parsley leaf oil and terpinolene, apiol and myristicin (Orav et al., seed oil. 192 G. Daradkeh and M.M. Essa

HO OH OH HO O

O C O O HO HO

OH OH O

Fig. 16.4. The chemical structure of apiin. From Hostetler et al., 2013.

Table 16.2. Composition of commercial samples of used with four extractions and 50:50 etha- parsley essential oil. Adapted from Charles, 2004. nol:water, was the best method. Second, Luthria (2008) examined the influence of six Compounds Leaf oil (%) Seed oil (%) additional PLE parameters (particle size, ex- Apiol 0.27 18.32 traction temperature and pressure, flush vol- Elemicin 2.71 4.84 ume, static time, and solid:solvent ratio), 1,3,8-p-Mentha-triene 16.41 0.12 and showed that the phenolic compounds Myrcene 4.24 0.22 obtained were influenced by temperature, Myristicin 11.92 39.65 particle size and solid:solvent ratio, with tem- α-Phellandrene 0.51 0.12 perature having the major effect on the phen- β-Phellandrene 6.48 2.14 olic profile (Luthria, 2008). When the extrac- -Pinene 26.42 15.73 α tion temperature was higher, malonyl apiin β-Pinene 18.04 10.01 Sabinene 1. 1 0.64 was partially degraded to acetylapiin and apiin, Terpinolene 2.52 0.01 while flush volume showed marginal influ- 2,3,4,5-Tetramethoxy- 0.72 7.82 ence on the extracted yield (Luthria, 2008). allylbenzene

16.3.2 Minimal processing 16.3 Postharvest Technology Fresh plant food can either be minimally 16.3.1 Extraction of phenolic compounds processed or not further processed at all prior to consumption. In a test of the storage Plant phenolics have several health benefits, of fresh parsley, leaves were sealed in poly- including: antioxidant, anti-inflammatory, ethylene bags and stored at 4°C for 12 days. antimicrobial, antitumour and hepatoprotec- Quality characteristics colour, appearance tive activities (Rice-Evans et al., 1996; Middle- (succulence and firmness) and aroma ton et al., 2000; Hinneburg et al., 2006). They (odour, taste) were evaluated on a scale of 1 vary in structure from monomers to complex to 5 on the 1st, 5th, 8th and 12th days. The polymeric tannins, and their isolation from scores were used to produce life curves, plants involves various steps (including sam- from which it was estimated that minimally ple grinding, extraction, pre-concentration, processed parsley could stay fresh for a hydrolysis and derivatization) that it is period of 23 days (Ca˘tunescu et al., 2012). important to get right. Luthria and co-workers have investigated the process in dried parsley flakes. First (Luthriaet al., 2006), they 16.4 Uses evaluated the influence of extraction solv- ents and techniques, and the number of 16.4.1 Traditional/medicinal benefits extraction cycles on the quantity of phen- olic compounds obtained, and determined The medicinal benefits of parsley have been that pressurized liquid extraction (PLE), long known, and Hippocrates classified parsley Parsley 193

as a diuretic. Wine boiled with parsley was and water extracts of freeze-dried recommended in medieval times as a treat- and irradiated parsley leaves and stems. ment for arthritis and chest pain. Parsley was recommended to alleviate menstrual Anti-inflammatory properties symptoms in the 17th century (Lis-Balchin, 2006), and was documented as a laxative, Parsley has been traditionally used for the diuretic and quinine substitute by the US treatment of allergies and autoimmune and Pharmacopeia in 1850 (Castleman, 2009). chronic inflammatory disorders (Yousofiet al., Parsley infusions were used to treat and 2012). Tissue damage, neuropathological dis- regulate menstrual pain by Colombian immi- eases and autoimmune disorders may result grants in London (Ceuterick et al., 2008). from chronic activation of the immune system, Parsley has also been reported as beneficial and myristicin oil from parsley can reduce for postmenopausal women. the immune inflammation by inhibiting nitric The use of both parsley seed powder oxide, cytokine production and the release of and parsley juice have been reported for inflammatory proteins (Lee and Park, 2011). the stimulation of hair growth when used Yousofiet al. (2012) investigated the suppres- to massage the scalp, and also for the treat- sive effects of parsley essential oil on mouse ment and prevention of insect bites (Charles, splenocytes and macrophages, and found 2004). that it could suppress nitric oxide production and the immune functions of macrophages.

Antimicrobial effects

16.4.2 Pharmacological uses Parsley plays an important role in the defence mechanisms against microbes such as bac- Antioxidant properties teria and fungi. For example, Manderfeld et al. (1997) reported that photoactive cou- Parsley was reported to protect cells by de- marins from fresh and freeze-dried parsley creasing the ageing process due to its anti- leaves protected against various human patho- oxidant properties, with the major contribu- gens and food spoilage organisms in a photo- tors to its antioxidant activity being myristicin biological assay. and apiol (Chevallier, 1996; Taiz and Zeiger The addition of fresh parsley leaves to 1998). Parsley essential oil was found to have ‘Kareish’ cheese reduced the amount of yeast β-carotene bleaching and free radical scav- present within 2 h. Additionally parsley ex- enging activities. Apiol contributes more free tracts showed a significant inhibitory activity radical scavenging activity than myristicin, against Staphylococcus aureus and antibac- even though it is present at a lower concen- terial activity against other microbial flora tration (contrast Fig. 16.3, which shows the in the cheese (Wahba et al., 2010). methoxy electron donor groups of apiol, with Wong and Kitts (2006) reported on the the structure of myristicin shown in Fig. 16.2) antibacterial activities of methanol and water (Zhang et al., 2006). extracts of freeze-dried and irradiated parsley The high content of such as leaves and stems against Bacillus subtilis and apiin, other apigenin glycosides and , Escherichia coli. tocopherol, ascorbic acid and essential oils in parsley could encourage antioxidant activ- Diuretic effect ity and might decrease any harm caused by oxidation (Nielsen et al., 1999). Myristicin, The diuretic effect of parsley has long been which is found in parsley oil, activates glu- noticed in traditional medicine. More recently, tathione-S-transferase, which catalyses the Marczal et al. (1997) studied the action of glutathione in fighting against oxi- components of the diuretic effect of parsley. dized molecules (Ozsoy-Sacan et al., 2006; Also, in rat in vivo and in vitro experiments, Kolarovic et al., 2010). Kreydiyyeh and Usta (2002) found that Wong and Kitts (2006) reported on the parsley extracts increased the urine output/ antioxidant (and antibacterial) activities of day by inhibiting Na+-K+-ATPase, thus leading 194 G. Daradkeh and M.M. Essa

to an increased K+ concentration in the kid- haemostasis-inhibiting platelet aggregation ney lumen that leads to an osmotic water in human platelets. flow into the lumen and diuresis. The German Commission E has accepted Contraindications the use of parsley for the treatment of kidney stones (Charles, 2004), most likely because Parsley is best avoided by pregnant women the consumption of parsley tea can increase because its myristicin and apiol content urine output, although it is recommended may stimulate the uterus. The availability of not to exceed three cups of parsley seed tea these components in the leaves, stalks and a day (Kreydiyyeh and Usta, 2002). roots is lower than in the seed oil, so these are safe to consume. Those with allergies to Hypoglycaemic effect plants in the Apiaceae family should avoid all parsley components and constituents The hypoglycaemic effect of parsley has been (Castleman, 2009; Fig. 16.5). reported by various researchers. Studies in other plants suggested that terpenoids have Drug interactions the ability to enhance insulin for the stimula- tion of glucose disposal and exert their anti- Parsley is rich in vitamin K, which inter- diabetic actions via α-glucosidase modulation, feres with warfarin, so those who are taking a typical extra-pancreatic mechanism (Luo the blood thinner warfarin should monitor et al., 1999; Kumar et al., 2011). parsley intake closely (Heck et al., 2000). It has also been reported that coumarins Parsley should also be avoided by those and glucosides (as found in pars- on diuretic drugs, because it will exacerbate ley) act in the scavenging or quenching of the diuretic action of the drugs, thus increas- free radicals (Anand et al., 1981), and that ing urine output and possibly causing too parsley, also being a good source of vitamin much fluid loss, leading to dehydration, diz- C, would also be effective in preventing ziness and hypotension. the non-enzymatic glycosylation of proteins In studies on mice, Jakovljvic et al. (Afkhami-Ardekani et al., 2003). (2002) have reported on the effect of parsley juice on pharmacodynamic activity of drugs Hepatoprotective effect involving cytochrome P450 in their metab- olism (the hypnotic pentobarbital and the Ozsoy-Sacan et al. (2006) showed that pars- analgesics paracetamol and aminopyrine). ley has a hepatoprotective effect on the liver tissue of streptozotocin (STZ)-induced dia- betic rats by decreasing blood glucose and 16.5 Summary lipid peroxidation, along with elevating the level of liver glutathione. Parsley is used as a table garnish worldwide, but its heath-promoting uses are often ignored, Anti-platelet aggregating effect like its valuable medicinal effects. It has great demand in the food and cosmetic industries, Gadi et al. (2009) reported that parsley ex- and the expansion of its cultivation is of prime tract inhibited in vitro and ex vivo platelet importance. aggregation and prolonged bleeding time in rats. Later, Chaves et al. (2011) have iso- lated and identified the flavonoids api- Acknowledgement genin, apigenin-7-O-glucoside (cosmosiin) and apiin, and the coumarin 2″,3″-dihy- The support provided by Internal grant droxyfuranocoumarin (oxypeucedanin hy- from CAMS, Sultan Qaboos University (IG/ drate) from aqueous extracts of the leaves of AGR/FOOD/14/01) is highly acknowledged. flat-leaved parsley. The extract, and api- The authors state that there is no conflict of genin and cosmosiin, all interfered with interest in this article. Parsley 195

Parsley seed oil, myristicin and apiol

Pregnancy Cooking

Gastroenteritis, headache, kidney and Stimulate the uterus liver function

Fig. 16.5. Contraindications for parsley seed oil and seed oil components. From/after Castleman, 2009.

References

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